vestichИзвестия Национальной академии наук Беларуси. Серия химических наукProceedings of the National Academy of Sciences of Belarus, Chemical Series1561-83312524-2342The Republican Unitary Enterprise Publishing House "Belaruskaya Navuka"10.29235/1561-8331-2020-56-2-192-196vestich-583Research ArticleОРГАНИЧЕСКАЯ ХИМИЯORGANIC CHEMISTRYСинтез спин-меченых эмоксипина, метионина, о-анизидинаSynthesis of spin-labeled emoxypine, methionine, o-anisidineЛисовскаяМ. В.LisouskayaM. V.

Лисовская Марина Владимировна – мл. науч. сотрудник

ул. Академика Купревича, 5/2, 220141, Минск

Maryna V. Lisouskaya – Junior Researcher

5/2, Academician Kuprevich Str., 220141, Minsk

lisovskaya@iboch.byКотН. В.KotN. V.

Кот Наталья Васильевна – химик-фармацевт 1-й категории. Научно-производственный центр «ХимФармСинтез»

ул. Академика Купревича, 5/2, 220141, Минск

Natalya V. Kot – 1st category chemist-pharmacist, Scientific-Production Centre “ChemPharmSynthesis”

5/2, Academician Kuprevich Str., 220141, Minsk

kot@iboch.byИнститут биоорганической химии Национальной академии наук БеларусиInstitute of Bioorganic Chemistry of the National Academy of Sciences of Belarus202006062020562192196Copyright © Лисовская М.В., Кот Н.В., 20202020Лисовская М.В., Кот Н.В.Lisouskaya M.V., Kot N.V.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vestichem.belnauka.by/jour/article/view/583

Синтезированы спин-меченые (ацилированные 4-доксилпентановой кислотой) эмоксипин, метионин, о-анизидин. Полученные соединения охарактеризованы с помощью физико-химических методов исследования (спектроскопия ядерного магнитного резонанса, электронного парамагнитного резонанса, инфракрасная и ультрафиолетовая спектроскопия и масс-спектрометрия). Синтезированные спин-меченые соединения могут быть использованы для биохимических исследований с помощью ЭПР-спектроскопии.

Spin-labeled (acylated with 4-doxylpentanoic acid) emoxypine, methionine, o-anisidine were synthesized. The compounds obtained were characterized using nuclear magnetic resonance spectroscopy, electron paramagnetic resonance spectroscopy, infrared and ultraviolet spectroscopy and mass spectrometry. Synthesized spin-labeled compounds can be used for biochemical studies using EPR spectroscopy.

нитроксильные радикалыспиновые метки4-доксилпентановая кислотаантиоксидантыэмоксипинметионино-анизидинЭПР-спектроскопияnitroxidesspin labels4-doxylpentanoic acidantioxidantsemoxypinemethionineо-anisidineEPR spectroscopyРабота поддержана Белорусским республиканским фондом фундаментальных исследований (договор № Х17М-104 от 18.04.2017 г.).This work has been supported by the Belarusian Republican Foundation for Fundamental Research (contract № X17M-104 dated 04/18/2017).ReferencesLewandowski, M. Nitroxides as Antioxidants and Anticancer Drugs / M. Lewandowski, K. Gwozdzinski // International Journal of Molecular Sciences, 2017. – Vol. 18, N 11. – P. 2490. https://doi.org/10.3390/ijms18112490Lewandowski M., Gwozdzinski K. Nitroxides as Antioxidants and Anticancer Drugs. International Journal of Molecular Sciences, 2017, vol. 18, no. 11, pp. 2490. https://doi.org/10.3390/ijms18112490Tabaczar, S. Nitroxides as antioxidants–Possibilities of their application in chemoprevention and radioprotection / S. Tabaczar, M. Talar, K. Gwozdzinski // Postępy Higieny i Medycyny Doświadczalnej, 2011. – Vol. 65. – P. 46–54. https://doi.org/10.5604/17322693.932256Tabaczar S., Talar M., Gwozdzinski K. Nitroxides as antioxidants – Possibilities of their application in chemoprevention and radioprotection. Postępy Higieny i Medycyny Doświadczalnej, 2011, vol. 65, pp. 46–54. https://doi.org/10.5604/17322693.932256Do nitroxide antioxidants act as scavengers of О2 -• or as SOD mimics? / M. C. Krishna [et al.] // The Journal of Biological Chemistry, 1996. Vol. 271, N 42. – P. 26026–26031. https://doi.org/10.1074/jbc.271.42.26026Krishna M. C., Russo A., Mitchell J. B., Goldstein S., Dafni H., Samuni A. Do nitroxide antioxidants act as scavengers of О2 -• or as SOD mimics? The Journal of Biological Chemistry, 1996, vol. 271, no. 42, pp. 26026–26031. https://doi.org/10.1074/jbc.271.42.26026Superoxide reaction with nitroxides / A. Samuni [et al.] // Free Radical Research Communications, 1990. – Vol. 9, N 3–6. – P. 241–249. https://doi.org/10.3109/10715769009145682Samuni A., Krishna M.C., Mitchell J. B., Collins C., Russo A. Superoxide reaction with nitroxides. Free Radical Research Communications, 1990, vol. 9, no. 3–6, pp. 241–249. https://doi.org/10.3109/10715769009145682SOD-like activity of 5-membered ring nitroxide spin labels/ A. Samuni [et al.] // Advances in Experimental Medicine and Biology, 1990. – Vol. 264. – P. 85–92. https://doi.org/10.1007/978-1-4684-5730-8_12Samuni A., Krishna M. C., Mitchell J. B., Russo A. SOD-like activity of 5-membered ring nitroxide spin labels. Advances in Experimental Medicine and Biology, 1990, vol. 264, pp. 85–92. https://doi.org/10.1007/978-1-4684-5730-8_12Keana, J. New Aspects of Nitroxide Chemistry/ J. Keana // Spin Labeling II: Theory and Applications / J. Keana; edited by L. J. Berliner. − Cambridge, Massachusetts: Academic Press, 2013. − 374 p.Keana J. New Aspects of Nitroxide Chemistry. Spin Labeling II: Theory and Applications. Cambridge, Massachusetts, Academic Press, 2013. 374 p.Keana, J. Newer Aspects of the Synthesis and Chemistry of Nitroxide Spin Labels / J. Keana // Chemical Reviews, 1978. – Vol. 78, N 1. – P. 37–62. https://doi.org/10.1021/cr60311a004Keana J. Newer Aspects of the Synthesis and Chemistry of Nitroxide Spin Labels. Chemical Reviews, 1978, vol. 78, no. 1, pp. 37–62. https://doi.org/10.1021/cr60311a004Joseph, J. Synthesis of a spin-labeled phospholipid for studying membrane dynamics in intact mammalian cells / J. Joseph, C.-S. Lai // Journal of Lipid Research, 1988. – Vol. 29, N 8. – P. 1101–1104.Joseph J., Lai C.-S. Synthesis of a spin-labeled phospholipid for studying membrane dynamics in intact mammalian cells. Journal of Lipid Research, 1988, vol. 29, no. 8, pp. 1101–1104.Fellmann, P. Synthesis and Use of Spin-Labeled Lipids for Studies of the Transmembrane Movement of Phospholipids /Fellmann P., Zachowski A., Devaux P. F. Synthesis and Use of Spin-Labeled Lipids for Studies of the Transmembrane Movement of Phospholipids. Biomembrane Protocols. Totowa, NJ, Humana Press Inc., 1994, pp. 161–175. https://doi.org/10.1385/0-89603-250-7:161Тихонов, А. Н. Спиновые метки / А. Н. Тихонов // Соросов. образоват. журн. − 1998. − № 1. − С. 8–15.Tikhonov А. Spin labels. Sorosovskii obrazovatel’nyi zhurnal [Soros Educational Journal], 1998, no. 1, pp. 8–15 (in Russian).

The authors declare that there are no conflicts of interest present.